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Dan Humphrey

Dan Humphrey is a romantic whose imagination runs wildly at the worst times. He over-analyzes life and can grow easily frustrated.

This young hunk is best friends with Vanessa Abrams (Jessica Szohr) and the big brother of Jenny Humphrey (Taylor Momsen).

Dan Humphrey has been head over heels in love with socialite Serena van der Woodsen for many years, and finally snagged his dream girl in the first season of Gossip Girl.

The adorable pair soon began dating and - after some initial difficulties - made love for the first time on Christmas.

However, their differences in social class - as well as her shady past and characters like Georgina Sparks - have driven them back apart.

An aspiring writer and fairly straight-arrow guy with a good heart and morals, Dan maintains his close relationship with his sister, Jenny and his father Rufus. He does not really fit in with Nate or Chuck, though he and the former seem to get along better than he does with the latter.

Blair: Fashion is the most powerful art there is. It's movement, design and architecture all in one. It shows the world who we are and who we'd like to be. Just like your scarf suggests that you'd like to sell used cars.Dan: Vanessa gave me this scarf.

[to Jenny] That's the thing. You need to be cool to be queen. Anne Boleyn thought only with her heart and she got her head chopped off. So her daughter Elizabeth made a vow never to marry a man. She married a country. Forget boys. Keep your eye on the prize, Jenny Humphrey. You can't make people love you, but you can make them fear you. For what it's worth, you're my Queen. I choose you.